Sodium Hydroxide → 2-ethyl-1H-indole

HRID 74589Notes

Reaction equation

HRID 74589 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH2:19][CH3:20])(=O)=O)C=CC=CC=1.[OH-].[Na+]>CCO>[CH2:19]([C:11]1[NH:10][C:18]2[C:13]([CH:12]=1)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 100167951H-Indole, 2-ethyl-1-(phenylsulfonyl)-

Product 1

HCID 38016182-ethyl-1H-indole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.2 g (4.2 mmol) 1-benzenesulphonyl-2-ethyl-1H-indole in 10 mL EtOH were combined with 5 mL of a (20 mmol) 4 N aqueous sodium hydroxide solution and refluxed for 8 h. Then the solvent was eliminated using the rotary evaporator and the residue was diluted with ice water. After acidifying with semi-concentrated aqueous hydrochloric acid the grease precipitated was extracted with ethyl acetate. The organic phase was dried on sodium sulphate, filtered off, evaporated down and dried.

Workup

  1. temperaturerefluxed for 8 h
  2. customthe rotary evaporator
  3. additionthe residue was diluted with ice water
  4. customprecipitated
  5. extractionwas extracted with ethyl acetate
  6. customThe organic phase was dried on sodium sulphate
  7. filtrationfiltered off
  8. customevaporated down
  9. customdried

Sources & evidence

ORD record
ord-003399a254d34568b19bee9374dea228
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

Loading…